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Simple Efficient Synthesis of Strongly Luminescent Polypyrene with Intrinsic Conductivity and High Carbon Yield by Chemical Oxidative Polymerization of Pyrene
Author(s) -
Li XinGui,
Liu YouWei,
Huang MeiRong,
Peng Sai,
Gong LingZhi,
Moloney Mark G.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902621
Subject(s) - polymerization , pyrene , chemistry , conductivity , yield (engineering) , monomer , quantum yield , luminescence , nuclear chemistry , photochemistry , inorganic chemistry , polymer , fluorescence , organic chemistry , materials science , physics , quantum mechanics , metallurgy , optoelectronics
A wholly aromatic polypyrene was synthesized by direct chemical oxidative polymerization of pyrene with ferric chloride as oxidant in hexane/nitromethane. Successful synthesis of polypyrene was thoroughly confirmed by IR, UV/Vis, 1D 1 H NMR, 2D 1 H– 1 H COSY, 2D 1 H– 13 C HSQC, MALDI‐TOF MS, elemental analysis, and X‐ray diffraction methods. The results indicated that the polypyrene was formed mainly through dehydro coupling between 2‐ or 1‐ and 2′‐ or 1′‐positions on pyrene rings having a degree of polymerization of around 24. The polypyrene was purified and then separated into THF‐soluble (ca. 10 %) and THF‐insoluble (ca. 90 %) fractions. Compared with insulating pyrene monomer, the polypyrene is a controllably conducting polymer that has low conductivity of 3.4×10 −8 S cm −1 in its virgin state, moderate conductivity of 2.28×10 −4 S cm −1 upon iodine doping, but much higher conductivity of up to 81.2 S cm −1 after the insoluble polypyrene was heated up to 1300 °C in nitrogen with a high char yield of 70.6 %. In particular, the soluble polypyrene demonstrates much stronger visible color fluorescence and much lower toxicity than pyrene. The soluble polypyrene would be advantageous for detecting Fe 3+ with almost no interference of other metal ions. The soluble and insoluble polypyrene fractions have potential applications as intrinsically luminescent and highly conducting carbon materials, respectively.